THE SYNTHESIS AND IN VITRO SCREENING OF THE 2-/3-ALKOXYPHENYLCARBAMIC ACID DERIVATIVES CONTAINING A 4 '-(2 '-FLUOROPHENYL)PIPERAZIN-1 '-YL MOIETY AGAINST SOME NON-TUBERCULOUS MYCOBACTERIAL STRAINS

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16170%2F17%3A43876157" target="_blank" >RIV/62157124:16170/17:43876157 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/62157124:16370/17:43876157

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

THE SYNTHESIS AND IN VITRO SCREENING OF THE 2-/3-ALKOXYPHENYLCARBAMIC ACID DERIVATIVES CONTAINING A 4 '-(2 '-FLUOROPHENYL)PIPERAZIN-1 '-YL MOIETY AGAINST SOME NON-TUBERCULOUS MYCOBACTERIAL STRAINS

Popis výsledku v původním jazyce

The current research was focused on the synthesis of 2-/3-alkoxyphenylcarbamic acid derivatives 5a-5d containing a salt-forming 4 &apos;-(2 &apos;-fluorophenyl)piperazin-1 &apos;-y1 moiety and their in vitro antimycobacterial investigation. Chemical structures of prepared intermediates and final compounds, which were isolated as salts with hydrochloric acid, were confirmed by the IR, H-1 NMR, and C-13 NMR spectral data. In addition, the target molecules 5a-5d were characterized by the MS as well as elemental analyses readouts. The final salts were in vitro screened against Mycobacterium marinum CAMP 5644, M. kansasii DSM 44162, M. smegmatis ATCC 700084 and M. avium subsp. paratuberculosis CIT03, respectively. The isoniazid, rifampicin and ciprofloxacin reference drugs were tested under the same experimental conditions as well. It was observed that both 3-alkoxy substituted derivatives 5c and 5d have shown the most promising potential against the M. kansasii strain with the M/C values of 145 mu mol.L-1 (molecule 5c) and 70 mu mol-L-1 (5d), respectively. In the light of the structure-antimycobacterial activity relationships study, it was found that an alkoxy chain attached to the 3-position and its elongation (therefore, an increase in lipophilicity) were considered favorable structural and physicochemical requirements rather than the presence of the 2-alkoxy group. Those conclusions were consistent with the findings from previous in vitro screening of those compounds against another atypical mycobacterium, M. kansasii CNCTC My 235/80. The electronic, steric and lipohydrophilic properties of the substituent attached to a 4 &apos;-(substituted phenyl)piperazin-1 &apos;-y1 fragment and its impact on the activity against given mycobacteria could be regarded as fairly comprehensive.

Název v anglickém jazyce

THE SYNTHESIS AND IN VITRO SCREENING OF THE 2-/3-ALKOXYPHENYLCARBAMIC ACID DERIVATIVES CONTAINING A 4 '-(2 '-FLUOROPHENYL)PIPERAZIN-1 '-YL MOIETY AGAINST SOME NON-TUBERCULOUS MYCOBACTERIAL STRAINS

Popis výsledku anglicky

The current research was focused on the synthesis of 2-/3-alkoxyphenylcarbamic acid derivatives 5a-5d containing a salt-forming 4 &apos;-(2 &apos;-fluorophenyl)piperazin-1 &apos;-y1 moiety and their in vitro antimycobacterial investigation. Chemical structures of prepared intermediates and final compounds, which were isolated as salts with hydrochloric acid, were confirmed by the IR, H-1 NMR, and C-13 NMR spectral data. In addition, the target molecules 5a-5d were characterized by the MS as well as elemental analyses readouts. The final salts were in vitro screened against Mycobacterium marinum CAMP 5644, M. kansasii DSM 44162, M. smegmatis ATCC 700084 and M. avium subsp. paratuberculosis CIT03, respectively. The isoniazid, rifampicin and ciprofloxacin reference drugs were tested under the same experimental conditions as well. It was observed that both 3-alkoxy substituted derivatives 5c and 5d have shown the most promising potential against the M. kansasii strain with the M/C values of 145 mu mol.L-1 (molecule 5c) and 70 mu mol-L-1 (5d), respectively. In the light of the structure-antimycobacterial activity relationships study, it was found that an alkoxy chain attached to the 3-position and its elongation (therefore, an increase in lipophilicity) were considered favorable structural and physicochemical requirements rather than the presence of the 2-alkoxy group. Those conclusions were consistent with the findings from previous in vitro screening of those compounds against another atypical mycobacterium, M. kansasii CNCTC My 235/80. The electronic, steric and lipohydrophilic properties of the substituent attached to a 4 &apos;-(substituted phenyl)piperazin-1 &apos;-y1 fragment and its impact on the activity against given mycobacteria could be regarded as fairly comprehensive.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

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Návaznosti

V - Vyzkumna aktivita podporovana z jinych verejnych zdroju

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Fresenius Environmental Bulletin

ISSN

1018-4619

e-ISSN

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Svazek periodika

26

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

12

Strana od-do

2759-2770

Kód UT WoS článku

000400806100036

EID výsledku v databázi Scopus

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